Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study

Cannatelli, Mark D.; Ragauskas, Arthur J.

doi:10.1016/j.tetlet.2016.07.016

Title: Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study

Abstract

The biocatalytic synthesis of phenothiazones and related compounds has been achieved in an aqueous system under mild conditions facilitated by laccase oxidation. It was found that by coupling 2-aminothiophenol directly with 1,4-quinones, the product yields could be significantly increased compared to generating the 1,4-quinones in situ from the corresponding hydroquinones via laccase oxidation. However, laccase still proved to be pivotal for achieving highest product yields by catalyzing the final oxidation step. Furthermore, a difference in reactivity of aromatic and aliphatic amines toward 1,4-naphthoquinone is observed. Furthermore, this study provides a sustainable approach to the synthesis of a biologically important class of compounds.

Authors:

Cannatelli, Mark D. ^[1]; Ragauskas, Arthur J. ^[2]

Georgia Inst. of Technology, Atlanta, GA (United States)
Georgia Inst. of Technology, Atlanta, GA (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Univ. of Tennessee, Knoxville, TN (United States)

Publication Date:: Wed Jul 06 00:00:00 EDT 2016

Research Org.:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Joint Institute for Biological Sciences (JIBS)

Sponsoring Org.:: USDOE Office of Science (SC)

OSTI Identifier:: 1327722

Grant/Contract Number:: AC05-00OR22725

Resource Type:: Accepted Manuscript

Journal Name:: Tetrahedron Letters

Additional Journal Information:: Journal Volume: 57; Journal Issue: 33; Journal ID: ISSN 0040-4039

Publisher:: Elsevier

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; biocatalysis; green chemistry; laccase; phenothiazones; thiol-amine

Citation Formats


                    Cannatelli, Mark D., and Ragauskas, Arthur J. Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study.  United States: N. p., 2016. 
Web.  doi:10.1016/j.tetlet.2016.07.016.

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                    Cannatelli, Mark D., & Ragauskas, Arthur J. Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study.  United States.  https://doi.org/10.1016/j.tetlet.2016.07.016

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                    Cannatelli, Mark D., and Ragauskas, Arthur J. Wed .  
"Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study".  United States.  https://doi.org/10.1016/j.tetlet.2016.07.016.  https://www.osti.gov/servlets/purl/1327722.

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@article{osti_1327722,

  title        = {Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study},

  author       = {Cannatelli, Mark D. and Ragauskas, Arthur J.},

  abstractNote = {The biocatalytic synthesis of phenothiazones and related compounds has been achieved in an aqueous system under mild conditions facilitated by laccase oxidation. It was found that by coupling 2-aminothiophenol directly with 1,4-quinones, the product yields could be significantly increased compared to generating the 1,4-quinones in situ from the corresponding hydroquinones via laccase oxidation. However, laccase still proved to be pivotal for achieving highest product yields by catalyzing the final oxidation step. Furthermore, a difference in reactivity of aromatic and aliphatic amines toward 1,4-naphthoquinone is observed. Furthermore, this study provides a sustainable approach to the synthesis of a biologically important class of compounds.},

  doi          = {10.1016/j.tetlet.2016.07.016},

  journal      = {Tetrahedron Letters},

  number       = 33,

  volume       = 57,

  place        = {United States},

  year         = {Wed Jul 06 00:00:00 EDT 2016},

  month        = {Wed Jul 06 00:00:00 EDT 2016}

}

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Title: Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study

Abstract

Citation Formats

The use of enzymes in organic synthesis and the life sciences: perspectives from the Swiss Industrial Biocatalysis Consortium (SIBC) journal, January 2013

Use of Enzymes in the Manufacture of Active Pharmaceutical Ingredients—A Science and Safety-Based Approach To Ensure Patient Safety and Drug Quality journal, September 2012

Redox Reactions Catalyzed by Isolated Enzymes journal, July 2011

How to enjoy laccases journal, January 2015

Potential applications of laccase-mediated coupling and grafting reactions: A review journal, March 2011

Laccases: a never-ending story journal, October 2009

Spatial structures of ascorbate oxidase, laccase and related proteins: implications for the catalytic mechanism book, June 1997

Concerted Electron/Proton Transfer Mechanism in the Oxidation of Phenols by Laccase journal, October 2013

O2 Reduction to H2O by the multicopper oxidases journal, January 2008

Shall We Dance? How A Multicopper Oxidase Chooses Its Electron Transfer Partner journal, June 2007

Fungal laccases – occurrence and properties journal, March 2006

The structure and function of fungal laccases journal, January 1994

Bacterial laccases journal, November 2006

Oxidative conjugation of catechols with proteins in insect skeletal systems journal, January 2001

Laccase: new functions for an old enzyme journal, July 2002

LXIII.—Chemistry of lacquer (Urushi). Part I. Communication from the Chemical Society of Tokio journal, January 1883

First description of a laccase-like enzyme in soil algae journal, July 2010

Biobleaching chemistry of laccase-mediator systems on high-lignin-content kraft pulps journal, February 2004

Investigations into Laccase-Mediator Delignification of Kraft Pulps journal, September 1999

Laccase-assisted surface functionalization of lignocellulosics journal, April 2014

Modification of high-lignin softwood kraft pulp with laccase and amino acids journal, March 2009

Evaluating laccase-facilitated coupling of phenolic acids to high-yield kraft pulps journal, June 2002

Laccase-based biosensors for detection of phenolic compounds journal, December 2015

Laccase and Laccase-Mediated Systems in the Synthesis of Organic Compounds journal, February 2014

Synthetic Applications of Laccase in Green Chemistry journal, June 2009

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One-Pot Laccase-Catalysed Synthesis of 5,6-Dihydroxylated Benzo[ b ]furans and Catechol Derivatives, and Their Anticancer Activity journal, February 2013

Laccase—a natural source for the synthesis of benzofuro[2,3-c]pyrazolin-5-ones journal, January 2013

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Studien in der Methylenblaugruppe journal, January 1885

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The Effect of Ferrivine and Intramine on Syphilis. journal, June 1916

2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and Biological evaluation as potential antiproliferative and antifungal agents journal, March 2009

Naphtho[2,3-b][1,4]-thiazine-5,10-diones and 3-substituted-1,4-dioxo-1,4-dihydronaphthalen-2-yl-thioalkanoate derivatives: Synthesis and biological evaluation as potential antibacterial and antifungal agents journal, November 2006

A Study of Cysteamine Ionization in Solution by Raman Spectroscopy and Theoretical Modeling journal, November 2006

The E Factor: fifteen years on journal, January 2007

The atom economy--a search for synthetic efficiency journal, December 1991

Dioxygen Activation by Laccases: Green Chemistry for Fine Chemical Synthesis journal, May 2018

The use of enzymes in organic synthesis and the life sciences: perspectives from the Swiss Industrial Biocatalysis Consortium (SIBC)
journal, January 2013

Use of Enzymes in the Manufacture of Active Pharmaceutical Ingredients—A Science and Safety-Based Approach To Ensure Patient Safety and Drug Quality
journal, September 2012

Redox Reactions Catalyzed by Isolated Enzymes
journal, July 2011

How to enjoy laccases
journal, January 2015

Potential applications of laccase-mediated coupling and grafting reactions: A review
journal, March 2011

Laccases: a never-ending story
journal, October 2009

Spatial structures of ascorbate oxidase, laccase and related proteins: implications for the catalytic mechanism
book, June 1997

Concerted Electron/Proton Transfer Mechanism in the Oxidation of Phenols by Laccase
journal, October 2013

O2 Reduction to H2O by the multicopper oxidases
journal, January 2008

Shall We Dance? How A Multicopper Oxidase Chooses Its Electron Transfer Partner
journal, June 2007

Fungal laccases – occurrence and properties
journal, March 2006

The structure and function of fungal laccases
journal, January 1994

Bacterial laccases
journal, November 2006

Oxidative conjugation of catechols with proteins in insect skeletal systems
journal, January 2001

Laccase: new functions for an old enzyme
journal, July 2002

LXIII.—Chemistry of lacquer (Urushi). Part I. Communication from the Chemical Society of Tokio
journal, January 1883

First description of a laccase-like enzyme in soil algae
journal, July 2010

Biobleaching chemistry of laccase-mediator systems on high-lignin-content kraft pulps
journal, February 2004

Investigations into Laccase-Mediator Delignification of Kraft Pulps
journal, September 1999

Laccase-assisted surface functionalization of lignocellulosics
journal, April 2014

Modification of high-lignin softwood kraft pulp with laccase and amino acids
journal, March 2009

Evaluating laccase-facilitated coupling of phenolic acids to high-yield kraft pulps
journal, June 2002

Laccase-based biosensors for detection of phenolic compounds
journal, December 2015

Laccase and Laccase-Mediated Systems in the Synthesis of Organic Compounds
journal, February 2014

Synthetic Applications of Laccase in Green Chemistry
journal, June 2009

Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones
journal, September 2015

Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones
journal, May 2015

One-Pot Laccase-Catalysed Synthesis of 5,6-Dihydroxylated Benzo[ b ]furans and Catechol Derivatives, and Their Anticancer Activity
journal, February 2013

Laccase—a natural source for the synthesis of benzofuro[2,3-c]pyrazolin-5-ones
journal, January 2013

Derivatization of amino acids by fungal laccases: Comparison of enzymatic and chemical methods
journal, September 2009

Novel β-Lactam Antibiotics Synthesized by Amination of Catechols Using Fungal Laccase
journal, January 2008

Nuclear Amination Catalyzed by Fungal Laccases: Reaction Products of p -Hydroquinones and Primary Aromatic Amines
journal, March 2005

Synthesis of 3-(3,4-dihydroxyphenyl)-propionic acid derivatives by N-coupling of amines using laccase
journal, September 2002

Enzymatic thiol Michael addition using laccases: Multiple CS bond formation between p-hydroquinones and aromatic thiols
journal, April 2016

Laccase-catalyzed synthesis of catechol thioethers by reaction of catechols with thiols using air as an oxidant
journal, January 2014

Laccase-Catalyzed CS and CC Coupling for a One-Pot Synthesis of 1,4-Naphthoquinone Sulfides and 1,4-Naphthoquinone Sulfide Dimers
journal, March 2013

A one-pot synthesis of 1,4-naphthoquinone-2,3-bis-sulfides catalysed by a commercial laccase
journal, January 2012

Laccase-Catalyzed Domino Reaction between Catechols and 6-Substituted 1,2,3,4-Tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles for the Synthesis of Pyrimidobenzothiazole Derivatives
journal, July 2013

Laccase enzyme catalysed efficient synthesis of 3-Substituted-1,2,4-triazoto(4,3-b)(4,1,2)benzothiadiazine-8-ones
journal, March 1994

The Effect of some Oxidation Products of Phenothiazine on Liver Fluke (Fasciola Hepatica) in Vitro
journal, June 1952

Studien in der Methylenblaugruppe
journal, January 1885

Über Phenthiazone I. Chlor-phenthiazone und deren Leukoverbindungen
journal, July 1958

Ueber die Constitution der Oxzin und Thiazinfarbstoffe und ihre Beziehungen zu den Azoniumkörpern
journal, January 1902

Über Phenothiazone, XVII1). Darstellung von Monomethyl-3H-phenothiazinonen-(3)
journal, April 1971

Oxidation of Phenols, Anilines, and Benzenethiols by Fungal Laccases: Correlation between Activity and Redox Potentials as Well as Halide Inhibition ^†
journal, January 1996

The Effect of Ferrivine and Intramine on Syphilis.
journal, June 1916

2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and Biological evaluation as potential antiproliferative and antifungal agents
journal, March 2009

Naphtho[2,3-b][1,4]-thiazine-5,10-diones and 3-substituted-1,4-dioxo-1,4-dihydronaphthalen-2-yl-thioalkanoate derivatives: Synthesis and biological evaluation as potential antibacterial and antifungal agents
journal, November 2006

A Study of Cysteamine Ionization in Solution by Raman Spectroscopy and Theoretical Modeling
journal, November 2006

The E Factor: fifteen years on
journal, January 2007

The atom economy--a search for synthetic efficiency
journal, December 1991

Dioxygen Activation by Laccases: Green Chemistry for Fine Chemical Synthesis
journal, May 2018